Yet as anyone who has made it through his books knows, he offers new and possibly profound insights into our world. The books covered here, which made him famous, are actually part of what he considers a single, four volume work. One of these volumes is a collection of philosophy and aphorisms and which by the end of this post I am sure you will not be surprised to hear that I skipped. The other three works, Fooled by Randomness , The Black Swan , and Antifragile  all contain at their cores some very important lessons for Achieving Sustainability.
Economists are organized; had they been isolated almost every one of them would be put in a mental hospital for hallucinations/dementia.— Nassim NicholنTaleb (@nntaleb) March 3, 2015
Fooled by Randomness The title says it all. Taleb describes how humans do not see randomness well (or at all), instead we create causality and narratives to explain inherent randomness. His background is in Wall Street, thus most of his examples are from the financial sector, an ideal hunting ground. An easy example you can see still persists on any financial news homepage where they announce that X news caused the market to go up or down--i.e. inventing causality to explain what are really random daily variations in stock market prices. Understanding the sectors where randomness dominates is hard because us humans seem biologically programmed to ignore it but we cannot if we hope to Achieving Sustainability.
The Black Swan In his most commercially successful book, Taleb proposes that very rare and extreme events are what drive history. He argues that these "Black Swan" events are effectively unpredictable because they are so rare. Yet afterwards we (humans) always come up with a narrative explanation about why and how this event came to happen. We then implement policies which we believe will prevent this Black Swan event from happening again. This, Taleb believes, is very foolish as the next history-changing event is sure to be some totally different Black Swan. Essentially he is saying we can't learn from past Black Swans and we can't hope to predict future ones (in their specifics, but we can be sure they will happen). Instead we have to create robust societies and institutions, or in the words of those in Sustainability circles, Resilience.2)A short introduction including seven principles. 
Antifragile In his final volume, Taleb pushes so far that he is forced to invent his own word, Antifragile. The subtitle sums up the idea: "Things that gain from disorder." Taleb contends that 1) many, many things gain from constant small stressors, 2) in the modern world we have removed these small stressors, 3) this has made our society very, very fragile. This is actually a strong argument as there are numerous cases to point to such as over-cleaning make us sicker, running on uneven surfaces making you less likely to be injured 3)Sensibly, this book is a favorite of an old running colleague of mine ., or trees that are tied down and not able to blow in the wind actually being far weaker and more prone to breaking . Unfortunately his attempt to extrapolate these specific examples into a broad general theory for societal organization is unconvincing at best. Yet we must absorb the lesson that a Sustainable future does not mean eliminating randomness, unpredictability and stressors--these things make society stronger, us happier and life more interesting.
3 Things I Liked
- People besides academics can advance science: We live too much in a world where one is either a full-time and therefore somewhat isolated "scientist" or working in the "real world" where one would never dream of doing science. We need to build up the middle--people who move up and back between academic and non-academic institutions already exists, particularly in fields like economics, but our Sustainable future needs more than that. We need anyone who has the inclination, interest, integrity and rigor to be able to contribute to the scientific discourse. Taleb is just such a person4)And for all his bad mouthing of academics he is now one himself!, unfortunately he is a terrible ambassador for the cause but we can't let his grating personality (at least as judged by his written words) be an impediment to fostering a host of citizen scientists like him.5)This term has been used before to describe things like participating in the yearly Audubon bird count, but I mean something much more profound and independent.
- Embracing randomness: Much of our lives from the good to the bad is caused by randomness and we cannot control it while worrying about it will only turn our hair gray. Our brains don't want to see it and thus construct narratives whether as individuals or as societies. We need to stop, it only misleads us about the future. Randomness is not so bad.
- Ranging from theory to application: Taleb has an overabundance of disdain for most academic theorists, and in some cases I can't muster much disagreement. But importantly he does not disdain theory as a concept. He just hates theory that is not informed by practice and that in and of itself can't be applied in a useful way to improve practice. This is particularly important in Sustainability Science where we begin in the real world and develop theories which specifically must be solutions oriented and contribute to practice. Taleb is exemplary in moving along this continuum from practice to theory and back again.
3 Things I Didn't LikeWhat I powerfully and strongly disliked about these books can be summed up in two words: Writing Style. Unfortunately I found that the writing got less and less palatable in each book.
- Overconfidence in his genius: Julian Baggini in the Guardian said it well : "This is far from the only time when Taleb overstates his case, committing errors he attributes to others. His overconfidence, ironically, makes his arguments more fragile to refutation than they needed to be."6)The review in the NY Times agrees  "Unfortunately he delivers such lessons with bullying grandiosity and off-putting, self-dramatizing asides." His overconfidence (or perhaps his internal lack of it) is most apparent in the way that he peppers the books with gratuitous and unnecessary insults at other people from economists, to financial analysts, to journalists and everyone in between. The sad thing is that his arguments are strong enough to stand on there own if he'd let them.
- Silly anecdotes: Here is someone who tells us not to fall for narratives and story telling but instead to rely on data, filling his book with personal stories of weight lifting and made up(?) stories about characters such as 'Fat Tony'. I found these to only very rarely be helpful and illuminating and most often to be distracting, unnecessary and mostly a vehicle for him to either brag or insult someone. Below I graph a count of references to 'Fat Tony' as a proxy for the number of silly anecdotes.
- All the philosophizing: Now this may be a personal bias as I have never been partial to philosophy whether modern or ancient which contrasts quite sharply with Taleb's fetish for what he calls "the wisdom of the ancients."7)So much to our views on this diverge that this series of books actually contains a fourth volume dedicated wholly to the ancients which I have skipped with no regrets. Now there was certainly wisdom then but I felt that its contribution to the thesis of these books required about 2% as many words. At best these long digressions were mere distractions but mostly they came off as him bragging about his classical education, vociferous reading habits and whatever other ability of his he wanted to feature in that section. The graph shows the number of references to the Roman philosopher Seneca as a proxy for space dedicated.
Aaron's ApprobationI wish with all my heart to recommend these books as required reading for all Sustainability students, so important do I feel are the main points of Taleb's books. If someone could remove all the silly anecdotes, philosophy digression, brags and insults, the books would not only be infinitely more readable and compact but Taleb's arguments would be many times more convincing and powerful. So if you are able to simultaneously steel yourself for insults and skim or skip often, you will be able to extract some very valuable juice from this trifecta of Taleb's.
Footnotes [ +  ]
|1.||↑||Interestingly enough this tweet has been deleted (by him?) but I shall preserve it here for posterity.|
|2.||↑||A short introduction including seven principles. |
|3.||↑||Sensibly, this book is a favorite of an old running colleague of mine .|
|4.||↑||And for all his bad mouthing of academics he is now one himself!|
|5.||↑||This term has been used before to describe things like participating in the yearly Audubon bird count, but I mean something much more profound and independent.|
|6.||↑||The review in the NY Times agrees  "Unfortunately he delivers such lessons with bullying grandiosity and off-putting, self-dramatizing asides."|
|7.||↑||So much to our views on this diverge that this series of books actually contains a fourth volume dedicated wholly to the ancients which I have skipped with no regrets.|